Ask middle managers to help articulate the “why” or business case for work flexibility in your organization, and then let them participate in determining what that flexibility will look like. Interview middle managers–the supporters of flexibility as well as the naysayers. Ask them why they think it is or is not important to be more flexible in the way work is done. Encourage them to tell you how it will solve their business challenges. Gather groups of managers and employees together to expand this shared vision they’ve created. At the end of the process, people feel invested in this approach to flexible work that they developed themselves.

Allow middle managers to freely express the “prices” they fear they will pay, while also helping them to focus on the payoffs of work flexibility. I love naysayers. When I am consulting to a group of managers about work flexibility and one of them has the courage to say, “Yeah, but I’m going to be left doing more work,” I want to hug them. They are articulating one of the very real fears many of the middle managers have about changing the way work is done. When you give middle managers a chance to share those concerns freely, they are able to move beyond them. They start to see the long list of benefits from having a more flexible approach to work. But if they can’t, they get stuck behind the fears.

Establish the expectation, at the beginning, that any issues related to work flexibility that cause the group not to meet its goals will be resolved by everyone, not just the manager. For example, a manager finds that having two people in the group teleworking from home on the same day causes difficulty with customer coverage. That manager would call the group together and ask them to help her come up with a way to solve the problem. She wouldn’t be expected to take it upon herself to make it work.

Rather than suggest that middle managers need “bootcamp” and to be browbeaten into accepting that the future of work at their firms is more flexible, Williams Yost takes a more respectful route that treats managers like concerned and frightened humans not thick-headed impediments. And who isn’t more persuaded by respectful dialogue than insulting hectoring? William Yost’s approach seems not only more humane but also more likely to be effective. Want more details? Her post is interesting throughout and well worth a read in full.

In an article in Businessweek, Michael Chertoff, former Secretary of Homeland Security gives an explanation of how to quickly get through the security checkpoints in an airport. His secrets include having your liquids and electronics accesible for easy removal and replacement. He also recommends having your change etc in your jacket pockets rather than your pants. That way you can lay the jacket, still loaded, in the tray, rather than rifling through your pants pockets.

I’m pretty good with security, but this article made me think, yet again, about optimisation. Smart people think about ways to improve every time single time they do something. Whether it’s a conversation or a physical skill or a process that has to be gone through, there’s a way to improve it.